Literature DB >> 20524618

Improved synthesis of enantiopure 4-hydroxy[2.2]paracyclophane.

Christian J Friedmann1, Sefer Ay, Stefan Bräse.   

Abstract

4-Hydroxy[2.2]paracyclophane is readily prepared via an improved synthetic protocol from unsubstituted [2.2]paracyclophane. The key step is a Dakin oxidation of 4-formyl[2.2]paracyclophane. This allows a rapid access to large quantities of the product and an easy synthesis of the enantiopure form.

Entities:  

Year:  2010        PMID： 20524618     DOI： 10.1021/jo100468s

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

Review 1.  Regioselective Functionalization of [2.2]Paracyclophanes: Recent Synthetic Progress and Perspectives.

Authors:  Zahid Hassan; Eduard Spuling; Daniel M Knoll; Stefan Bräse
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-30       Impact factor: 15.336

2.  Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane.

Authors:  David Weinzierl; Mario Waser
Journal:  Beilstein J Org Chem       Date:  2021-04-08       Impact factor: 2.883

3.  A small molecule screen identifies novel inhibitors of mechanosensory nematocyst discharge in Hydra.

Authors:  Diana Hofmann; Niharika Garg; Simone Grässle; Sylvia Vanderheiden; Bruno Gideon Bergheim; Stefan Bräse; Nicole Jung; Suat Özbek
Journal:  Sci Rep       Date:  2021-10-18       Impact factor: 4.379

4.  Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands.

Authors:  Sundaravel Vivek Kumar; Patrick J Guiry
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-09       Impact factor: 16.823

5.  Fluorescence detected circular dichroism (FDCD) for supramolecular host-guest complexes.

Authors:  Amrutha Prabodh; Yichuan Wang; Stephan Sinn; Paolo Albertini; Christian Spies; Eduard Spuling; Liu-Pan Yang; Wei Jiang; Stefan Bräse; Frank Biedermann
Journal:  Chem Sci       Date:  2021-06-09       Impact factor: 9.825
  5 in total

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